| fluopyram |
 |
Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home
GENERAL INFORMATION 
for fluopyram
Description: Novel broad spectrum fungicide for use as a foliar application and as a seed treatment to control various diseases. Also has nematicide activity.
Example pests controlled: Botrytis, Powdery mildew, Fusarium virguliforme
Example applications: Potatoes; Sugarbeet; Fruit including apples, grapes and strawberries; Cotton
Efficacy & activity: -
Availability status: Current
Introduction & key dates: 2008
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Denmark |
| Date inclusion expires | 31/01/2024 |
| EU Candidate for substitution (CfS) | No |
| Listed in EU database | Yes |
Approved for use (
) or known to be used (
) in the following European countries: 
AT |
BE |
BG |
CY |
CZ |
DE |
DK |
EE |
EL |
ES |
FI |
FR |
HR |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
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Also used in: First registrations expected in 2011
Chemical structure:
| Isomerism | - |
| Chemical formula | C16H11ClF6N2O |
| Canonical SMILES | C1=CC=C(C(=C1)C(=O)NCCC2=C(C=C(C=N2)C(F)(F)F)Cl)C(F)(F)F |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | KVDJTXBXMWJJEF-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C16H11ClF6N2O/c17-12-7-9(15(18,19)20)8-25-13(12)5-6-24-14(26)10-3-1-2-4-11(10)16(21,22)23/h1-4,7-8H,5-6H2,(H,24,26)/f/h24H |
| 2D structure diagram/image available? | Yes |
General status:
| Pesticide type | Fungicide, Nematicide | |||
| Substance group | Benzamide, pyramide | |||
| Minimum active substance purity | 960 g/kg | |||
| Known relevant impurities | EU dossier - none declared | |||
| Substance origin | Synthetic | |||
| Mode of action | Succinate Dehydrogenase Inhibitor. | |||
| CAS RN | 658066-35-4 | |||
| EC number | - | |||
| CIPAC number | 807 | |||
| US EPA chemical code | 080302 | |||
| PubChem CID | 11158353 | |||
| Molecular mass (g mol-1) | 396.76 | |||
| PIN (Preferred Identification Name) | N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide | |||
| IUPAC name | N-[2-[3-chloro-5-(trifluoromethyl)-2-pyridyl]ethyl]-α,α,α-trifluoro-ortho-toluamide | |||
| CAS name | N-(2-(3-chloro-5-(trifluoromethyl)-2-pyridinyl)ethyl)-2-(trifluoromethyl)benzamide | |||
| Other status information | - | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | 7 | |||
| Examples of recorded resistance | - | |||
| Physical state | - | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
|
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| Example products using this active |
|
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| UK LERAP status | Buffer probably required in UK - see product label | |||
| Formulation and application details | Both seed treatments and suspension concentrate products for foliar application are available. | |||
ENVIRONMENTAL FATE
for fluopyram
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 16.0 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 250000 | A5 - Acetone | - | |
| 250000 | A5 - Dichloromethane | - | ||
| 660 | A5 - n-Heptane | - | ||
| 62200 | A5 - Toluene | - | ||
| Melting point (oC) | 117.5 | A5 | - | |
| Boiling point (oC) | 318 | A5 | - | |
| Degradation point (oC) | 300 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 2.00 X 1003 | Calculated | - |
| Log P | 3.3 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | - | - | - | |
| Dissociation constant (pKa) at 25oC | Not applicable | A5 | - | |
| Note: No dissociation | ||||
| Vapour pressure at 20oC (mPa) | 1.2 X 10-03 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 2.98 X 10-05 | A5 | Non-volatile | |
GUS leaching potential index  |
3.23 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 4.46 X 10-01 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | 216nm=14877, 270nm=4332, 290nm<10 | A5 | - | |
| Surface tension (mN m-1) | 59.4 | A5 | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 309 | A5 | Persistent |
| DT50 (lab at 20oC) | 309 | A5 | Persistent | |
| DT50 (field) | 118.8 | A5 | Persistent | |
| DT90 (lab at 20oC) | 723 | A5 | - | |
| DT90 (field) | 833 | A5 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU dossier lab studies DT50 range 117-717 days, DT90 range 538->1000 days, Field studies DT50 range 93.2-144.6 days, DT90 range 487->1000 days | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 6.5 | R4 | - |
| Note | Published literature RL50 range 4.0-9.0 days, various matrices from 3 crops grown in field & undercover, n=3 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | 21 | A5 | Slow |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | A5 | - |
| Note | Stable at pH 5, 7 & 9 @ 50 Deg C | |||
| Water-sediment DT50 (days) | 1077 | A5 | Stable | |
| Water phase only DT50 (days) | 20.5 | A5 | Slow | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | - | - |
| Koc | - | |||
| Notes and range | - | |||
| Freundlich | Kf | 4.41 | A5 | Moderately mobile |
| Kfoc | 278.9 | |||
| 1/n | 0.827 | |||
| Notes and range | EU dossier Kf range 2.94-6.83 mL/g, Kfoc range 233-400 mL/g, 1/n range 0.765-0.948, Soils=6 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| N-(2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-hydroxyethyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10065) | Soil | 0.042 | Minor fraction, Not relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| N-(2-(3-chloro-1-oxide-5-(trifluoromethyl)pyridin-2-yl)ethyl))-2-(trifluoromethyl)benzamide Note: MWt=412.72 |
AE C656948-N-oxide | Plants | - | - |
| - | AE C656948-enol-GA | Rat | - | - |
| - | AE C656948-phenol | Animal | - | - |
| - | AE C656948-phenol-glc | Rat | - | - |
| - | AE C656948-phenol-GA | Animal; Rat | - | - |
| - | AE C656948-benzamide | Animal; Rat; Plants; Soil | - | - |
| 1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)benzoyl)amino)ethyl beta-D-glucopyranosiduronic acid Note: MWt=588.85 |
AE C656948-7-OH-GA | Animal; Fish; Rat | - | - |
| 1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)phenyl)carbonyl)amino)ethyl hydrogen sulfate Note: MWt=492.78 |
AE C656948-7-OH-SA | Plants | - | - |
| N-(2-(3-chloro-5-(trifluoromethyl)pyridine-2-yl)-2-(beta-D-glucopyranosyloxyethyl)-2-(trifluoromethyl) benzamide Note: MWt=574.87 |
AE C656948-7-hydroxy-glc | Plants | - | - |
| 1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-((2-trifluoromethyl)benzoyl)amino)ethyl beta-D-glucopyranoside Note: MWt=660.91 |
AE C656948-7-hydroxy-glc-MA | Plants | - | - |
| - | AE C656948-7-OH-phenol | Rat | - | - |
| - | AE C656948-7-OH-phenol-GA | Rat | - | - |
| - | AE C656948-7-OH-phenol-SA | Rat | - | - |
| - | AE C656948-7-OH-methyl-sulfone | Rat | - | - |
| - | AE C656948-7-OH-hydroxyphenol-SA | Rat | - | - |
| N-(2-(3-chloro-1-oxide-5-(trifluoromethyl)pyridin-2-yl)-1-hydroxyethyl)-2-(trifluoromethyl)benzamide Note: MWt=412.72 |
AE C656948-8-hydroxy | Animal; Fish; Rat; Plants | - | - |
| - | AE C656948-di-8-OH-GA | Animal; Rat | - | - |
| - | AE C656948-hydroxy-glyc-gluc | Plant | - | - |
| - | AE C656948-methoxy-di-OH-GA | Rat | - | - |
| N-acetyl-O-(2-(trifluoromethyl)benzoyl)serine Note: MWt=319.24 |
AE C656948-benzoyl-serine | Rat | - | - |
| - | AE C656948-hydroxy-benzamide | Rat | - | - |
| - | AE C656948-benzamide-OH-GA | Rat | - | - |
| - | AE C656948-benzamide-cysteine | Rat | - | - |
| - | AE C656948-BA-methyl-sulfoxide | Rat | - | - |
| - | AE C656948-BA-methyl-sulfone | Rat | - | - |
| - | AE C656948-benzamide-SA | Rat | - | - |
| 1-O-((2-trifluoromethyl)benzoyl)amine)-beta-D-glucopyranuronic acid Note: MWt=365.3 |
AE C656948-benzamide-N,O-GA | Rat | - | - |
| 2-(trifluoromethyl)benzoic acid Note: MWt=190.12 |
AE C656948-benzoic acid | Rat; Plants | - | - |
| 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethanol Note: MWt=225.60 |
AE C656948-pyridyl-hydroxyethyl | Animals | - | - |
| 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethyl beta-D-glucopyranoside Note: MWt=387.3 |
AE C656948-hydroxyethyl-glc | Plants | - | - |
| - | AE C656948-hydroxyethyl-di-glc | Plants | - | - |
| - | AE C656948-hydroxyethyl-GA | Animal; Rat | - | - |
| - | AE C656948-ethyl-diol | Rat | - | - |
| - | AE C656948-ethyl-diol-GA | Rat | - | - |
| - | AE C656948-pyrodyl-acetic acid | Animal; Rat; Plants | - | - |
| - | AE C656948-hydroxy-PAA | Animal; Rat | - | - |
| - | AE C656948-PAA-glycoside | Plant | - | - |
| - | AE C656948-pyridyl-methyl-cystein | Rat | - | - |
| 3-chloro-2-methyl-5-(trifluoromethyl)pyridine Note: MWt=195.57 |
AE C656948-picoline | - | - | - |
| 1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-1-((2-(trifluoromethyl)benzoyl)amino)ethyl 6-O-(carboxyacetyl)-beta-D-glucopyranoside Note: MWt=660.91 |
AE C656948-8-hydroxy-glc-MA | Plants | - | - |
| 2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-1-((2-(trifluoromethyl)benzoyl)amino)ethyl)-beta-D-glucopyranosiduronic acid Note: MWt=588.85 |
AE C656948-8-OH-GA | Animal; Fish; Rat | - | - |
| 3-(methylsulfinyl)-5-(trifluoromethyl)pyridine-2-carboxylic acid (Ref: AE 1344122) Note: MWt=253.20 |
AE C656948-methyl-sulfoxide | Plants; Soil | - | - |
| (Ref: AE C657188) Note: MWt=225.26 |
AE C656948-pyridyl-carboxylic acid | Rat; Plants; Soil | - | - |
| N-((E)-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethenyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10627) Note: MWt=394.71 |
AE C656948-N-olefine | Animals | - | - |
| (Ref: BCS-AA10634) Note: MWt=360.26 |
AE C656948-lactame | Photolysis | - | - |
| N-((Z)-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)ethenyl)-2-(trifluoromethyl)benzamide (Ref: BCS-AA10650) Note: MWt=394.71 |
AE C656948-Z-olefine | Animals | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 18 | A5 Whole fish | Low potential |
| CT50 (days) | 3.4 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 2000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | - | - | - |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginians | Low | |
| Birds - Short term dietary (LC50/LD50) | > 1643 mg/Kg BW/day | A5 Anas platyrhynchos | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 0.98 | A5 Coleonyx variegatus | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.135 | A4 Pimephalis promelas, 33 day | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | > 100 | A5 Daphnia magna | Low | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 1.25 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | 2.32 | A5 |
Moderate | |
| Non-target plants | > 0.25 | A5 Fagopyrum esculentum Seedling emergence, ER50 as g/ha |
- | |
| > 0.50 | A5 Beta vulgais Vegetative vigour, ER50 as g/ha |
- | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | > 1.13 | A5 Skeletonema costatum | Moderate | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees (Apis spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 100 | A5 Apis mellifera | Low |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | > 102.3 | A5 Apis mellifera | Low | |
| Unknown mode acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Bumblebees (Bombus spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| - | ||||
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| - | ||||
| Mason bees (Osmia spp.) | Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - |
| Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) | - | - | - | |
| Other pollinators (1) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Other pollinators (2) | Acute LD50 (worst case from 24 , 48 and 72 hour values - μg insect-1) | - | - | - |
| Mode of exposure | - | |||
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 1000 | A5 Eisenia foetida | Low | |
| Earthworms - Chronic NOEC, reproduction (mg kg-1) | 11.42 | A5 Eisenia foetida | Moderate | |
| Other soil macro-organisms | Acute LC50 (mg kg-1) | - | - | - | Chronic NOEC (mg kg-1) | 103.8 | A5 Folsomia candida | - |
| Other arthropod (1) | LR50 g ha-1 | 2000 | > A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | 2000 | > A5 Aphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effects Carbon mineralisation: No significant adverse effect |
A5 Dose: 3.33 mg kg-1 soil, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for fluopyram
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | > 2000 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 5.11 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.012 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.5 | A5 Rat, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | - | - | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.05 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 1-3 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Routes | Public | Acceptable for intended uses | ||
| Occupational | Acceptable for intended uses | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Genotoxic | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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A3; B0; C3; D0; E0 | - |
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- |
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
- |
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| General human health issues | Possible liver, thyroid and blood toxicant | |||||||
| Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative |
Key: Other : Yes, known to cause a problem  : No, known not to cause a problem  : Possibly, status not identified - : No data found |
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Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Not oxidising or explosive IMDG Transport Code is usually 9 |
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| CLP classification 2013 | Environment: H411 | |||
| EC Risk Classification |
N - Dangerous for the environment: R51/53 | |||
| EC Safety Classification |
- | |||
| WHO Classification | NL | - | Not listed | |
| UN Number | 3077 | |||
| Waste disposal & packaging |
Packaging Group III (minor danger) | |||
| Language | Name |
| English | fluopyram |
| French | - |
| German | - |
| Danish | - |
| Italian | - |
| Spanish | - |
| Greek | - |
| Slovenian | - |
| Polish | - |
| Swedish | fluopyram |
| Hungarian | - |
| Dutch | - |
Record last updated: Friday 15 November 2019
Contact: aeru@herts.ac.uk
© University of Hertfordshire